This is an image from Chesapeake Painting Services, located in Maryland. The logo for Chesapeake Painting Services features a stylized paint roller design with a bowtie shape beside the company name in blue and green text.

Chesapeake Painting Services

This is an image from Chesapeake Painting Services, located in Maryland. The logo for Chesapeake Painting Services features a stylized paint roller design with a bowtie shape beside the company name in blue and green text.
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Chooz Score Insights

Scored by
Almira A.
Ed Anthony D.
January 2026

Familiar Faces, Consistent Results

What sets this company apart is their consistent crew. The Chooz Score's in-house crews component shows the same crew names appearing across multiple reviews, suggesting trained, dedicated employees rather than rotating subcontractors:

  • Mike, Jeremia, Jose, Emmanuel, Byron, and Yvonny appear by name across different customer projects
  • Known locally as "The Gentlemen Painters" for their professional demeanor
  • Repeat customers like Debbie Powers note this is her "third project" with consistent results

"I cannot say enough positive things about my experience with Chesapeake Painting. From getting an estimate all the way through completing the job, the communication was outstanding as was the quality of work." - Kathy K., Google Review

Find out more about how we Chesapeake Painting Services

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All verified feedback is published, positive or not. Identity and project verified before publication. Direct submissions are unpaid; invited customers may receive a disclosed $50 thank-you that never depends on their answers.

Additional Questions Answered

How does Chesapeake Painting Services handle century-old cedar shake homes?

Barry describes their work on his "100 year old cedar shake home" as "outstanding," calling the team "timely, professional, flexible." Robert continues to "use them for painting and other fix-ups around our historic home." Sandy mentions extensive renovation in their "historical house" across multiple rooms. The crew understands original millwork preservation, period-appropriate surface treatments, and careful handling of aging materials. Projects include cedar shake tile replacement, fascia repair, and restoration work requiring experienced craftsmanship beyond standard residential painting.

Source: Google Reviews · Reviewed April 2026
Does Chesapeake Painting Services maintain consistent communication throughout projects?

Kathy calls out estimator Mike and painters Jeremia and Jose, stating "communication was outstanding" and they were "constantly checking in to see if I had any questions all through the project." Elyse describes the team as "super communicative" from estimate through completion. Tom mentions working with Mike was "an absolute pleasure" and the crew "patiently answered all our questions." The structure includes estimator consultations, daily crew updates, project manager check-ins, and owner oversight ensuring accessibility from initial contact through final walkthrough.

Source: Google Reviews · Reviewed April 2026
What makes Chesapeake Painting Services' cleanup practices different from other contractors?

Kim describes them as "extremely clean" and notes "they clearly take pride in their work." Tami highlights how painters "cleaned up everyday" and when finished, "put everything back together how it originally was. Right down to the decor and throw pillows." Dave mentions the crew "cleaned up well each night" when working around existing construction. Elyse states they "worked clean" throughout her project. The daily site cleanup, furniture protection, and final restoration demonstrate thoroughness that customers contrast with previous contractor experiences.

Source: Google Reviews · Reviewed April 2026
Why do customers praise Chesapeake Painting Services' cabinet refinishing results?

Karen mentions they did an "excellent job color matching" between her island and existing cabinets, calling the crew "meticulous." Edward states the "finish on the cabinets is perfect." Tami describes how her cabinets "look great," noting she "could not be more pleased with the results." Ali explains their kitchen project left them "SO happy" because the team "guided us through the process seamlessly." The preparation work, spray application technique, and factory-quality finish transform kitchens without replacement costs, with customers noting the precision and durability.

Sources: Google Reviews, Yelp · Reviewed April 2026
Does Chesapeake Painting Services consistently meet project deadlines?

Tom explains the crew not only met their tight deadline before vacation but "finished with plenty of time to spare." Bobbi thanks painters Emmanuel and Byron for getting work "finished ahead of time." Sarah notes that although initially quoted four to six weeks, the company "found a way to fit us in within 2 weeks without us having to ask." Cathy mentions they "worked me into their busy schedule so that my house was painted before I moved in." The reliability stems from realistic estimates and efficient crew management.

Source: Google Reviews · Reviewed April 2026
How did Chesapeake Painting Services address the negative review about poor workmanship?

Elizabeth raised concerns about workmanship quality, lack of final walkthrough, and unresponsive quality control after sending detailed photos. The company offered to send the crew back, though Elizabeth declined further disruption. This contrasts with Dave mentioning Chesapeake "proactively followed up with me to conduct a job completion walk-through," noting many contractors "try to avoid a walk-through when the job is finished." The pattern suggests walkthrough protocols exist but weren't followed in Elizabeth's case, showing inconsistency in quality control execution.

Source: Google Reviews · Reviewed April 2026
Does Chesapeake Painting Services use in-house employees or rotating subcontractors?

Reviews mention painters by name across different timeframes. Kathy worked with Mike, Jeremia, and Jose. Bobbi had Emmanuel and Byron. Tom's project was led by Yvonny. Courtney's intricate floor design was completed by Jeremiah. Christopher notes his second major project maintained quality, stating the team is "genuinely 'The Gentlemen Painters.'" The consistent crew names and company branding suggest W2 employees with stable assignments rather than rotating subcontractors, allowing customers to build relationships with painters across multiple projects.

Sources: Google Reviews, Yelp · Reviewed April 2026
How does the Blue Star merger affect Chesapeake Painting Services operations?

The companies merged and relocated to 146 Defense Highway in Annapolis, combining capabilities while preserving service approaches. One customer notes starting with a Chesapeake estimate but receiving a Blue Star crew, creating "a few crossed wires at the beginning," though project manager Sebastian "immediately came out" to resolve issues and "then everything ran smoothly." The transition showed some coordination challenges during the merger period. Current operations integrate both teams under unified management, with the combined entity offering expanded services across residential and commercial sectors.

Sources: Google Reviews, Company Website · Reviewed April 2026
How Chesapeake Painting Services Was Evaluated

Every painting company listed on Chooz Painters is evaluated using our multi-step quality framework. We combine structured data analysis with human review to understand how Chesapeake Painting Services performs across the key signals that matter most to property owners.

How the Chooz Score Works

The Chooz Score is a 100-point rating based on four core pillars:

  • Platform reviews & ratings from sources such as Google, Facebook, Yelp, Angi, BBB, and others
  • Review quality & engagement, including depth of customer feedback, photos, and how the company responds to reviews
  • Website and digital presence, which helps indicate professionalism, transparency, and communication quality
  • Business authority & operations, including years in business, licensing, insurance, and other operational standards

Each contractor is evaluated using the same framework nationwide, and the score reflects Chesapeake Painting Services’s performance within its local market.

A Chooz Score represents real-world performance, verified signals, and human-reviewed context.

Chooz Score Award Levels

80–86.9: Chooz Certified87–93.9: Top Painter Award94–100: Best Painter Award

Scores are determined through more than 40 evaluation factors across our four pillars.

If you want a deeper explanation of how our scoring system works, you can view the full breakdown on our Chooz Scoring page.